Bob Flanagan grew up with cystic fibrosis (a congenital, nearly always–fatal disease). He died at the age of 43, one of the oldest people with the disease. The physical pain of his childhood suffering was principally alleviated by masturbation and sexual experimentation, where pain and pleasure became inextricably linked, resulting in his lifelong practice of extreme masochism. In deeply confessional interviews, Bob details his sexual practices and his extraordinary relationship with long-term partner and Mistress, photographer Sheree Rose. Through his insider's perspective on the Sado-Masochist community, we learn firsthand about branding, piercing, whipping, bondage, and endurance trials. These extreme narratives are infused with humor, honesty, and self-reflective irony.